| Record Information |
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| Version | 1.0 |
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| Creation Date | 2009-03-06 18:58:30 UTC |
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| Update Date | 2016-11-09 01:08:12 UTC |
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| Accession Number | CHEM000262 |
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| Identification |
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| Common Name | [4-(Aminocarbonyl-amino)phenyl] arsonic acid |
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| Class | Small Molecule |
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| Description | [4-(aminocarbonyl-amino)phenyl] arsonic acid is an arsenic-based antiprotozoal drug which has been used in the treatment of infections. |
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| Contaminant Sources | - IARC Carcinogens Group 3
- T3DB toxins
- ToxCast & Tox21 Chemicals
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| Contaminant Type | - Amine
- Aromatic Hydrocarbon
- Arsenic Compound
- Food Toxin
- Industrial/Workplace Toxin
- Organic Compound
- Organometallic
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| [4-(Aminocarbonyl-amino)phenyl] arsonate | Generator | | Carbarson | MeSH | | 4-Ureidobenzenearsonic acid | MeSH | | Carbason | MeSH |
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| Chemical Formula | C7H9AsN2O4 |
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| Average Molecular Mass | 260.079 g/mol |
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| Monoisotopic Mass | 259.978 g/mol |
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| CAS Registry Number | 121-59-5 |
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| IUPAC Name | [4-(carbamoylamino)phenyl]arsonic acid |
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| Traditional Name | carbarsone |
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| SMILES | NC(=O)NC1=CC=C(C=C1)[As](O)(O)=O |
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| InChI Identifier | InChI=1S/C7H9AsN2O4/c9-7(11)10-6-3-1-5(2-4-6)8(12,13)14/h1-4H,(H3,9,10,11)(H2,12,13,14) |
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| InChI Key | WWXBHTZSYYGCSG-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as n-phenylureas. N-phenylureas are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | N-phenylureas |
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| Direct Parent | N-phenylureas |
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| Alternative Parents | |
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| Substituents | - N-phenylurea
- Pentaorganoarsane
- Carbonic acid derivative
- Urea
- Organic metalloid salt
- Oxygen-containing organoarsenic compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organic salt
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organoarsenic compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | No data. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 174°C | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Toxicity Profile |
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| Route of Exposure | Oral (3) ; inhalation (3); dermal (3) |
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| Mechanism of Toxicity | Arsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carcinogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (2, 1) |
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| Metabolism | Arsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (4) |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (5) |
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| Uses/Sources | [4-(aminocarbonyl-amino)phenyl] arsonic acid was used as a drug to treat infections. It is now found in poultry feed and used to treat some avian diseases. |
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| Minimum Risk Level | Acute Oral: 0.005 mg/kg/day (6)
Chronic Oral: 0.0003 mg/kg/day (6)
Chronic Inhalation: 0.01 mg/m3 (6) |
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| Health Effects | Hypovolemia from capillary leakage (third-spacing of fluids) is a common, serious, early effect. Muscle cramps, facial edema, bronchitis, dyspnea, chest pain, dehydration, intense thirst, and fluid-electrolyte disturbances are also common following significant exposures. A garlic-like odor of the breath and feces may also occur. After absorption, arsenic may cause multi-organ failure by inhibiting sulfhydryl-containing enzymes. Encephalopathy, with headache, lethargy, mental confusion, hallucinations, emotional lability, memory loss and delirium may occur; seizures, stupor, convulsions, coma, and death may follow within 24 hours of a severe acute exposure. Dysrhythmias (particularly QTc prolongation and torsade de pointes), cardiomyopathy, ARDS, hepatitis, rhabdomyolysis, hemolysis, and renal failure may develop over several days. The sequence of chronic poisoning involves hyperpigmentation, and eczematoid and allergic dermatitis. muscle fasciculations; gross tremors; ataxia; incoordination; and mental confusion. Muscular weakness, limb tenderness and difficulty walking may follow. The final phase consists of peripheral sensory neuropathy of the hands and feet. That may be associated with a motor neuropathy as well . |
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| Symptoms | Initial signs and symptoms of arsenic ingestion include burning lips, throat constriction and dysphagia, followed by excruciating abdominal pain, hemorrhagic gastritis, gastroenteritis, severe nausea, projectile voting, profuse "rice water-like" diarrhea, with hypovolemia that may result in hypotension and an irregular pulse. The sequence of chronic poisoning involves weakness, anorexia, hepatomegaly, jaundice, and gastrointestinal complaints, followed by conjunctivitis, irritation of the throat and respiratory tract. ther effects of chronic exposure include conjunctivitis with irritation and lacrimation; hair, skin and nail changes; hyperkeratosis of feet and hands; and melanosis, with pigment spots in corneal and conjunctival epithelium. Peripheral nervous system symptoms may include numbness, burning, and tingling of the hands and feet; pain; paresthesias; tenderness . |
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| Treatment | Aggressive decontamination with gastric lavage is recommended if the patient has consumed a potentially life-threatening dose and if the patient is not vomiting . |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB11382 |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 8480 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | Not Available |
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